A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Osprey condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is AED 249
AED 1,931 total
includes taxes & fees
9 Jul - 10 Jul
Chadwick Cove Resort & Marina
Beach nearby, beach towels

Waterfront Condo · Heated Pools · WiFi · Lanai · IMG Academy · Anna Maria Island

Waterfront Condo · Heated Pools · WiFi · Lanai · IMG Academy · Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (122 reviews)
"We loved the property, large pool & access to activities. "
United States
Mary Beth M.
The price is AED 454
AED 1,205 total
includes taxes & fees
31 Jul - 1 Aug
Waterfront Condo · Heated Pools · WiFi · Lanai · IMG Academy · Anna Maria Island
Marina

Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
Waterfront Condo Walkable to Everything with Beach Access
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is AED 507
AED 2,299 total
includes taxes & fees
9 Jul - 10 Jul
Cedar Run Resort - Roam Hospitality
Dining

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.2 out of 10, Wonderful, (82 reviews)
"Great location and great views!"
United States
Mark H.
The price is AED 691
AED 1,400 total
includes taxes & fees
15 Jul - 16 Jul
The Beach on Longboat Key #227 Resort by RVA
On the beach

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (103 reviews)
"Close to the beach. The bed could use some updating. "
United States
Joe B.
The price is AED 705
AED 1,410 total
includes taxes & fees
2 Aug - 3 Aug
Oceanfront Bliss–Longboat Key Beach 106 by RVA
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,279 reviews)
"Great spot for a weekend getaway."
United States
Tom
The price is AED 606
AED 747 total
includes taxes & fees
9 Jul - 10 Jul
Captiva Beach Resort
Property grounds

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock

Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
Manasota Key
9.8 out of 10, Exceptional, (48 reviews)
"Host was very communicative and helpful. "
United States
Jennifer O.
The price is AED 507
AED 1,325 total
includes taxes & fees
16 Jul - 17 Jul
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
On the beach, beach umbrellas

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (88 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful beach, would stay again."
United States
Michael M.
Silver Sands 1BR – Gulfside Comfort #255 by RVA
On the beach, beach umbrellas

Gulfside 2BR Condo–Silver Sands #257S

Gulfside 2BR Condo–Silver Sands #257S
Longboat Key
8.6 out of 10, Excellent, (35 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very pleasant quiet community"
United States
Patty B.
The price is AED 1,249
AED 2,424 total
includes taxes & fees
3 Aug - 4 Aug
Gulfside 2BR Condo–Silver Sands #257S
Interior

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN

Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
Bradenton
10.0 out of 10, Exceptional, (14 reviews)
"The place is cozy and conveniently located to IMG Academy. New appliances and very clean. There are chairs for the beach which is helpful; Coquina Beach is 20 mins away."
United States
Jen
The price is AED 496
AED 1,249 total
includes taxes & fees
9 Jul - 10 Jul
Near Beaches & Outdoor Activites! Relaxation and Fun! 2 BR/BA/LR & KITCHEN
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (81 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
Beachfront Studio – Cabana #5B by RVA
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (646 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is AED 607
AED 686 total
includes taxes & fees
3 Aug - 4 Aug
A Beach Retreat
On the beach, sun loungers, beach towels

3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf

3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (71 reviews)
"The view was amazing. House clean. Highly recommend!"
United States
Sarah S.
The price is AED 580
AED 1,546 total
includes taxes & fees
9 Jul - 10 Jul
3 Bedroom-Beach Front Condo w/ Beautiful Views of the Gulf
On the beach

Jetties Pointe Cottage #2 - 408 “Casey Key”

Jetties Pointe Cottage #2 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed walking out the door, through the patio, right on to the beautiful beach. Comfortable bed. Kitchen well equipped. A couple restaurants within walking distance over the bridge. Already missing the sunsets. "
United States
Stephanie B.
The price is AED 690
AED 1,560 total
includes taxes & fees
19 Jul - 20 Jul
Jetties Pointe Cottage #2 - 408 “Casey Key”
On the beach, beach umbrellas

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is AED 878
AED 1,643 total
includes taxes & fees
2 Aug - 3 Aug
1BR Beach Getaway – Silver Sands #254 by RVA
Beach nearby, sun loungers, beach towels

Spacious Condo w/Lanai · Two Pools & Hot Tubs · IMG Academy · Anna Maria Beaches

Spacious Condo w/Lanai · Two Pools & Hot Tubs · IMG Academy · Anna Maria Beaches
Bradenton
10.0 out of 10, Exceptional, (130 reviews)
"It was a perfect location, looked exactly like the pictures and the host did everything to make our stay great!"
United States
Martha B.
The price is AED 436
AED 1,185 total
includes taxes & fees
26 Jul - 27 Jul
Spacious Condo w/Lanai · Two Pools & Hot Tubs · IMG Academy · Anna Maria Beaches
On the beach

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (75 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
The price is AED 657
AED 1,357 total
includes taxes & fees
12 Jul - 13 Jul
Newly Renovated 1BR – Cabana Beach #5 RVA
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (81 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
The price is AED 841
AED 1,602 total
includes taxes & fees
6 Aug - 7 Aug
Relax at Gulf – Silver Sands Resort #232, Longboat
Terrace/patio

Turtle Nest

Turtle Nest
Sarasota
10.0 out of 10, Exceptional, (11 reviews)
"Check was smooth and easy and location was GREAT!"
United States
Annie S.
The price is AED 826
AED 2,195 total
includes taxes & fees
7 Aug - 8 Aug
Turtle Nest
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"The Hotel is clean, modern, quiet, safe. The staff was welcoming. Julio in the reception/ lobby was helpful and respectful. Very professional."
Ellimay 1-night trip
Posted 1 hour ago
Kompose Boutique Hotel

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from AED 686 to AED 2,424 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Osprey?
Choose from multiple condos in Osprey with a total average guest review rating of 9.4. Venice Beach Villas comes highly recommended if you're traveling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3614 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.
Are there any 5-star condos in Osprey?
Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 11 kilometers from the downtown area, Gulf Holiday By Beachside Management comes with concierge services and a swimming pool. Another upscale retreat is Excelsior Beach To Bay - Bayside. It's roughly 8 kilometers from the center of Osprey and has amenities like a swimming pool and a deck.
Why book your condo in Osprey with Expedia?
With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap condos in Osprey?
With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating.